Sodium Hydroxide → HCID 11644260, compound

HRID 985504Notes

Reaction equation

HRID 985504 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>Br.C(O)(=O)C>[CH3:18][C:16]1[CH:15]=[CH:14][N:13]2[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)=[CH:10][N:11]=[C:12]2[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11564945HCID 11564945, compound

Product 1

HCID 11644260HCID 11644260, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

A solution of 3-(3-methoxyphenyl)-7-methylimidazo[1,2-α]pyridine (19 g, 80 mmol) in hydrogen bromide (160 ml of a 45% w/v solution in acetic acid) was heated at reflux for 18 hours. The cooled reaction was poured into sodium hydroxide solution (800 ml of a 4M aqueous solution), the pH adjusted to 7 with acetic acid and the resulting cream-coloured solid filtered and dried under vacuum at 60° C. to yield 3-(7-methylimidazo[1,2-α]pyridin-3-yl)phenol (18 g, 95%). 1H NMR (400 MHz, CDCl3) δH 6.79-6.83 (2H, m), 6.96-7.01 (2H, m), 7.30-7.33 (1H, m), 7.41 (1H, s), 7.62 (1H, s), 8.42 (1H, d, J 7); m/z (ES+) 225 (M++H).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe cooled reaction
  3. filtrationthe resulting cream-coloured solid filtered
  4. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-75b2add942f846ba86744f6b873f544b
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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